Conformationally locked nucleosides. Synthesis and stereochemical assignments of 3′-N,5′-C-bridged 3′-amino-3′-deoxythymidines

✍ Scribed by Guangyi Wang

• Book ID: 104261988
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 226 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)01205-8

✦ Synopsis

3'-Amino-3'-deoxythymidine was converted, in multi-steps, to its 5'-O-(4,4'-dimethoxytrityl)-5'-C-tosyloxyethyl-3'-N-carbobenzoxy derivative 7 and 5'-C-mesyloxyethyl-3'-N-(9-fluorenyl)methoxycarbonyl derivatives 6 and 11. Subsequent hydrogenolysis or treatment with DMAP afforded 3'-N,5'-C-bridged bicyclic thymidines. Stereochemical assignments were accomplished with the help of NOE.